Sodium Bicarbonate → HCID 24772088, compound

HRID 1409532Notes

Reaction equation

HRID 1409532 reaction equation
[ClH:1].[CH3:2][O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].O.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[ClH:24].CN(C)[CH2:27][CH2:28][CH2:29][N:30]=[C:31]=[N:32][CH2:33][CH3:34].[C:36](=[O:39])([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[Cl:1][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:34]1[CH:33]=[N:32][C:31]2[N:30]([N:12]=[CH:6][C:4]=2[C:36](=[O:39])[NH:12][C:6]2([C:4]([O:3][CH3:2])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[C:29]=1[C:28]1[CH:27]=[CH:10][C:9]([Cl:24])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 24772088HCID 24772088, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the compound obtained in Reference Example 1-(4) (300 mg) and 1-methoxycarbonylcyclohexylamine hydrochloride (181 mg) in dichloromethane (4 mL) were added 1-hydroxybenzotriazole monohydrate (179 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (224 mg) and triethylamine (328 μL), and the mixture was stirred at room temperature overnight. To the reaction mixture were added methylene chloride and an aqueous saturated sodium hydrogencarbonate solution. After stirring vigorously for 10 minutes, the organic layer was separated and concentrated in vacuo. The resultant crude product was purified by column chromatography on NH-silica gel (Chromatorex NH silica gel, Fuji Silicia Chem., solvent; hexane/ethyl acetate=70/30 to 50/50) to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-[N-(1-methoxycarbonylcyclohexyl)carbamoyl]pyrazolo[1,5-a]pyrimidine (380 mg; yield: 93%).

Workup

  1. stirringAfter stirring vigorously for 10 minutes
  2. customthe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe resultant crude product was purified by column chromatography on NH-silica gel (Chromatorex NH silica gel, Fuji Silicia Chem., solvent; hexane/ethyl acetate=70/30 to 50/50)

Sources & evidence

ORD record
ord-5a1022f84a0240f08f01428186fbd002
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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